The Roaring Twenties were a time period filled with tales of adventure and glamour. Prohibition fueled a party lifestyle - and made available a dangerous but adrenaline fueled life to some of the more enterprising members of the underworld. In Chicago, Illinois, the Twenties have become a time of legend and usually call to mind one man, Al Capone. But Capone, for all intents and purposes, was only a figure head during the Beer Wars. He ran his gang and racket, but he delegated the dirty work.
To the north of him was a group that was, as one newspaper of the time called them, Modern Day Pirates, The North Side Gang. Consider Capone the Prince John to their Robin Hood and his Merry-men, an analogy that Rose Keefe introduced in her book, Guns and Roses: The Untold Story of Dean O’Banion. Robin Hood isn’t quite as steal from the rich to give to the poor and you’ll need to give Little John a temper and thirst for vengeance that was unrivaled. Also, make the merry-men a little crazier and a lot more deadly. You get the picture.
Hymie Weiss more than likely would look back at 1924 as one of those years where everything and anything just seemed to have gone wrong for him. It had all calumniated in the death of his best friend and mentor in November. When Dean O’Banion died, Hymie said everything he had in the world was gone. But that didn’t mean that he was going to stand by and let it stay that way. He mourned his friend, buried him and then began a campaign of vengeance.
Erin Finlen continues her series.
Part one is here.
Grave of Hymie Weiss at Mount Carmel Cemetery in Hillside, Illinois. Source: Nick Number, available here.
Childhood
West Division Street ran through the middle of the Polish neighborhood of Bucktown on the West Side of Chicago and at 2021 W. Division Street was a saloon that was run by William Wojciechowski and his wife Mary. The pair had moved from New York with their children, Joseph, Bernard, and Frederick. In Chicago, they welcomed another daughter named Violet. Then, on January 25, 1898, the youngest of their children, Henryk Josef Wojciechowski, was born, although he would later change his name to Earl, saying it sounded like royalty. His mother would eventually decide to Americanize their last name to Weiss, although not legally.
He was enrolled at a school, St. Malachy’s on Washington, where he, from all accounts was a smart child with lots of friends, adored by his teachers. One even gave him a pocket bible which he would carry in his pocket for the rest of his life. The influences of the saloon life ran deep, and in 1913 his oldest brother, Joseph, was arrested and charged in the murder of three men. According to Joseph and his father a fight had broken out and Joseph was acting in self-defense. He was acquitted. However, rumors soon started circulating in the newspapers that the trial had been fixed and Joseph moved to New Mexico, where he died from Tuberculosis. Whatever the effect this had on Jospeh’s younger siblings is hard to say, as at this time Henryk would have been sixteen and already involved in crime on his own. He had also taken the name Earl.
Hotheadedness and violence seemed to run in the family though, as William, his father was arrested and injured in a labor dispute in Buffalo, New York in 1894 and Fred, Earl’s brother, was also considered to have had a formidable temper as well.
For the most part though, young Earl was no different than most other boys his age, involved in street gang wars from the time he was ten. He wasn’t the healthiest and had suffered from headaches for a long time. In 1918, he tried to join the army but was denied, as his draft card says, for a “double rupture” in his heart. At the time, Weiss was angry, annoyed that he couldn’t serve his country with the skills he had earned on the street. History, though, had different plans for Earl Weiss.
The Making of an Outlaw
Weiss was not an outwardly friendly individual and he was even less adept at making friends with newspapermen, telling them, “If you take my picture, I swear I’ll kill you.” Making an enemy of the press had earned him a much hated nickname, “The Perfume Burglar,” after he tried to rob a store, knocked over the perfume counter and was arrested smelling strongly of multiple scents. Eventually, the press and the underworld gave him a new nickname, “Hymie,” because of his outwardly Jewish appearance, even though he was catholic. He didn’t mind the nickname and seems to have let it stick.
After being turned away from military service he turned his criminal pursuits to safe cracking with Charles Reiser, where he met his mentor and best friend, Dean O’Banion. As discussed in Dean’s article the pair were a study in opposites and while Weiss is often branded the temperamental one it was he that was better at thinking through his actions and planning ahead. Unless provoked, of course.
In June of 1920 he shot his brother, Fred, in their shared apartment for a joke his brother made about Hymie not serving in the military (while newspaper articles at the time say that Fred served in the army, I have yet to find anything besides his draft card and his headstone does not bare the veteran symbol). In a fit of anger he shot Fred square in the chest and then, took him to a nearby hospital before running away. Fred survived and begged the doctors to not look into, although they reported it to the police anyway. The police arrested Weiss, but were not able to find any evidence to convict him.
In the meantime, he was busy helping Dean build their bootlegging empire with their friends Vincent Drucci and George Moran. They were making enough money now to be able to bribe most cops and judges. While they were bootlegging, they continued to pursue other criminal activities. In 1922, Weiss and Moran, under his alias of George Nolan were arrested after a police chase for stealing jewels. No charges were ever pressed all the police did have to fire shots to get the pair to pull over.
Illness and Mourning
At the same time, Weiss was making regular use of the couch that Dean had placed in his office for him. The regular headaches that had plagued him all his life were growing more frequent and the pain getting so unbearable he once had a fit on the floor of the North Siders garage. In early 1924, he left Chicago for Hot Springs, Arkansas in hopes of improving his health. While away, his brother in law and Dean were placed under suspicion for the murder of John Duffy and his name was brought into the equation due to the car being in his name. There probably wasn’t much of the hoped for relaxing on the trip.
When he returned he received a devastating diagnosis, he had terminal arterial cancer. This had been causing the headaches and fainting for so long. It was also the cause of that double rupture that had kept him out of World War I. He was given around two years to live and he intended to make the most of them. He is quoted as saying, “I’m not going to live long, but I will live long enough.” He just had to deal with fallout from Sieben Brewery raid.
It is suspected that he was the real mastermind behind ending the Torrio treaty. He was the thinker of the group but whether he didn’t consider the consequences or simply didn’t think they would be so severe, he still found himself mourning the loss of his best friend in November of that year.
A lifetime of an impulsive temper and hard knocks had taught Weiss a thing or two about revenge and as he drove out of Dean O’Banion’s funeral he was determined to make the people who took him from him pay.
Love and War
Weiss waited and he planned. From November until January he gathered information and observed. Then on January 24, 1925, when Johnny Torrio and his wife pulled up outside their home after a shopping trip Weiss and Moran with Drucci driving the car pulled up next behind them. After waiting for Anna Torrio and the dog to be clear of the car they fired on Johnny Torrio, hitting him multiple times. When he fell to the ground, George Moran ran up to shoot the fatal shot when a laundry truck came around the corner and Drucci blew the horn: it was time to go. Thinking they had done enough damage the North Siders fled the scene. Anna Torrio, a nurse ran to her husband’s side and slowed the bleeding until ambulances arrived.
When word reached Hymie Weiss that he had not succeeded in eliminating Torrio, who was now in critical condition but very much alive in a hospital he was furious. One nurses account gives us an idea of how he reacted when the planning and intelligent part of his brain gave way to the impulsive and angry emotions. She told authorities that a man had run up to the desk demanding to know where Torrio was. She refused, saying no one was allowed to see him, Torrio’s wife had insisted on no one but family and an approved few friends. The man insisted and the nurse, thinking quickly, informed him that there was an increased police presence at the hospital. The man left in hurry after that. The nurse later identified the man as Earl “Hymie” Weiss from his mugshot.
1925 was not off to an auspicious start in anyway and in April, Weiss appeared in court for charges from a bootlegging arrest the previous year. Having originally made a plea of not guilty, he changed it to guilty and in May would serve six months at McHenry County Jail. He was still able to keep in touch and visit with the other members of the North Side Gang and by this time it had become clear that he was the new boss, through his intelligence and the charm that he did have but regularly chose not to use.
When he got out in the fall of 1925, the Genna Gang was no longer an issue, being eliminated through the police, Capone, and Drucci and Moran. He seemed to have relaxed a little and that could be because fell in love shortly after his release.
He met a Follies’ Girl by the name of Josephine Simard in the lobby of the Congress and the two immediately hit it off. He even followed her to New York when she left and returned with her now as husband and wife.
She was what Dean had been for him, a ray of sunshine to his dark moods and while they did fight often—the famous scene in “The Public Enemy” (1931) where James Cagney shoves a melon into Mae Wests face is supposedly based off of Hymie Weiss shoving an omelet in Josephine’s face when she wouldn’t stop talking one morning— they were a well matched pair and seemed very happy together.
He might have cooled in his quest for revenge but his temper certainly had not. In June of 1926, when he was at a party raided by police, he forced the policeman to leave at gun point. The police obviously came back with help and Weiss and a friend were arrested. Weiss wasn’t done yet and filed a petition to be reimbursed for items he believed were stolen during the raid. The petition was quickly denied, but it seems that it might have stirred something of the old Weiss in him.
The Battle Resumes
In August of 1925, Weiss and Drucci, who had been a massive thorn in the side for Al Capone for a while were attacked by rival gangsters and involved in a shoot-out in front of the Standard Oil Building. Well, Drucci was. Weiss ran for cover and Drucci hopped on the running boards of a passing car, telling the driver to follow the assailants, before he was nabbed by the cops. Weiss telephoned his mother, Mary Weiss, who showed up at the police station to pay Drucci’s bail. Drucci’s explanation to police for the event was the gangsters were trying to rob him.
Police and the North Siders weren’t fooled. It was the Capone gangsters as retribution for the killing of Al Capone’s chauffeur, who it was believed was kidnapped and tortured for information about Capone’s routine by the North Side Gang (Note: John Binder, in his book “Al Capone’s Beer Wars” posits that this was probably not the North Side Gang and I am inclined to agree: it did not fit with any of the other crimes committed by the gang under Weiss. Torture of those not directly involved with a life of crime was not their style. It was more likely the Saltis gang behind the chauffeur’s death).
For a month, Hymie Weiss, Vincent Drucci, and George Moran waited before their next attack. The audacity and publicity of the attack has gone down in history as one of the more dramatic gangland attacks of all time. On September 20, 1926 a parade of cars pulled up in front of the Hawthorne Hotel where Capone was having lunch. They fired a first volley of blank ammunition to draw Capone outside and then the real firing began. The mess of shooting used somewhere around two hundred bullets and witnesses agreed they saw Hymie Weiss and Moran or one of the Gusenberg Brothers get out and fire Tommy Guns into the restaurant. One of the Capone gunmen from the Standard Oil Shootout was injured and so was a woman eating in the restaurant. Capone paid for her hospital bills.
Capone decided to give peace talks one more try but not in person, he sent a liaison. Capone was famously scared of Weiss and it’s easy to see why. Capone was a man with a lot to lose and Weiss, as he saw it, had nothing. Weiss told the liaison that he would agree to peace if Capone surrendered John Scalise and Albert Anselmi, who he knew were involved in the murder of Dean O’Banion, to the North Siders. Capone refused and Weiss left the meeting angry.
October 11, 1926, Hymie Weiss’s car pulled up outside Holy Name Cathedral, with four of his men. As he was crossing the street bullets from Thompson SubMachine Gun burst from the window of a nearby apartment. Weiss fell to the ground unconscious and died on the way to the hospital. Paddy Murray, a fellow gangster was also killed and the other three men were critically injured. The side of the church was broken with machine gun bullets and streets away, when Vincent Drucci heard the news he was distraught and newspapers reported that he was being held back from attacking the perpetrators.
Saying Goodbye
Weiss’s funeral wasn’t quite as big as O’Banion’s, a fact that irritated Josephine Simard, but Moran tried to gently explain that they had lost several friends to violence over the last two years. Mary Weiss was accompanied by her two sons and sobbed next to the coffin.
In the fall of 1927, the will of Earl J. Weiss was called into question and while Josephine tried to stand her ground she was no match for the formidable Mary Weiss, who refused to relinquish anything except the car that had been gifted to her (and even that was on court orders) without a marriage certificate, which Josephine could not produce.
Left with two bosses to choose from, there was really only one person to step in after Hymie Weiss died, the man who had loved him as a brother and the one who was nicknamed Schemer for his crazy plans, Vincent Drucci.
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Sources
Binder, J. J. (2017). Al Capone’s Beer wars: A Complete History of Organized Crime in Chicago during Prohibition. Prometheus Books.
Burns, W. N. (1931). The one-way ride: The Red Trail of Chicago Gangland from Prohibition to Jake Lingle.
Keefe, R. (2003). Guns and roses: The Untold Story of Dean O’Banion, Chicago’s Big Shot Before Al Capone. Turner Publishing Company.
Keefe, R. (2005). The Man who Got Away: The Bugs Moran Story : a Biography. Cumberland House Publishing.
Kobler, J. (2003). Capone: The Life and World of Al Capone. Da Capo Press.
Sullivan, E. D. (1929). Rattling the cup on Chicago crime.
